Top 10 Best Winnie the Pooh Character Pairs

For most of my life, the Winnie the Pooh franchise has remained one of my absolute favorite series from my childhood. I still love it just as much today.

Here are the best pairs of characters that are absolutely the best when paired together. This is not in a shipping way, just in a friendly friendship sort of way. I don't ship any of the Winnie the Pooh characters together. This franchise and its characters are just much too close and dear to me to spoil in that way.

1. Pooh and Christopher Robin

   

   The timeless story of a boy and a bear. Can't get much better than this.

2. Pooh and Piglet

   

   Piglet is, and will most likely always remain, one of my favorite fictional characters ever created. (A bit of an odd choice, maybe. You tell me.) So it makes sense that he and his best friend, Winnie the Pooh Bear, would take the number one spot.

   Maybe I'm a bit biased. I'm sure I am. But I really think this is one of the best friendship pairings ever created. Piglet treats the dim and not-so-bright bear with a very little brain with equal respect, and Pooh helps him get over his constant fears and anxieties. Christopher Robin and Pooh are iconic, sure, and for a very good reason, but it just doesn't beat the brilliant chemistry these two very best friends share.

3. Tigger and Rabbit

   

   Two of the funniest characters paired together, and it took me decades to realize that Rabbit may be the first ever rabbit tsundere.

4. Tigger and Roo

   

   Tigger pretty much acts like a big brother toward Roo.

5. Piglet and Tigger

   

   A bouncing big guy and a shrinking little guy. Not much else to explain.

6. Pooh and Tigger

   

   I feel that their friendship was better in the later series than in the original, because Tigger kinda just pops in for a while and then just leaves.

7. Owl and Gopher

   

   Another hilarious pair. Who could forget their first encounter in Winnie the Pooh and the Honey Tree? And it's even better in The New Adventures series.

8. Rabbit and Gopher

   

   Not as well known as Owl and Gopher, but it was brought up several times in the later cartoon series. It makes sense that a rabbit and his garden would create an interesting relationship with a tunneling gopher.

9. Pooh and Rabbit

   

   When Rabbit finally warms up to this silly old bear, it proves just how good a friend Rabbit can be.

10. Tigger and Eeyore

    

    Two completely opposite personalities. One is charismatic, energetic, happy, and excited. The other is the exact opposite, to say the least.

    The best in the 2011 movie, when Tigger tries to help Eeyore train to become a second Tigger. It works out just about as well as you'd expect.

The Newcomers
11. ?

    Kanga and Roo

12. ?

    Tigger and Owl

The Contenders

13. Piglet and Eeyore

    

    An underrated pairing of friends, to be sure. Piglet always trying to cheer him up is always so sweet and sad at the same time.

14. Rabbit and Kessie